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Establishment of Breakthrough on Unactivated Alkane C-H Bond Amination

Research Project

Project/Area Number 24659006
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Chemical pharmacy
Research InstitutionThe University of Tokushima

Principal Investigator

OCHIAI Masahito  徳島大学, 大学院・ヘルスバイオサイエンス研究部, 教授 (50127065)

Project Period (FY) 2012
Project Status Completed (Fiscal Year 2012)
Budget Amount *help
¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2012: ¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Keywords有機化学 / CHアミノ化反応 / ナイトレノイド / 臭素 / 超原子価 / アルカン
Research Abstract

Our project involves a development of new research field “chemistry of hypervalent bromane”. We have developed a new methodology for direct regioselective alkane C-H amination, which involves in situ generation of iminobromane. Iminobromane generated from diacyloxybromane by the reaction with triflylamide in alkane as a solvent undergoes alkane C-H amination. Excellent regioselectivity as well as stereoselectivity were observed in the reaction.

Report

(2 results)
  • 2012 Annual Research Report   Final Research Report ( PDF )
  • Research Products

    (23 results)

All 2013 2012 Other

All Journal Article (3 results) (of which Peer Reviewed: 3 results) Presentation (18 results) (of which Invited: 1 results) Remarks (2 results)

  • [Journal Article] Time-lapse fluorescence imaging and quantitative single cell and endosomal analysis of peritoneal macrophages using fluorescent organosilica nanoparticles2013

    • Author(s)
      M. Nakamura, K. Miyamoto, K. Hayashi, A. Awaad, M. Ochiai, K. Ishimura
    • Journal Title

      Nanomedicine: Nanotechnology, Biology, and Medicine

      Volume: 9 Issue: 2 Pages: 274-283

    • DOI

      10.1016/j.nano.2012.05.018

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] A catalytic version of hypervalent aryl-λ3-iodane-induced Hofmann rearrangement of primary carboxamides: iodobenzene as an organocatalyst and m-chloroperbenzoic acid as a terminal oxidant2012

    • Author(s)
      Miyamoto K. et al.
    • Journal Title

      Chem. Commun.

      Volume: 48 Issue: 7 Pages: 982-984

    • DOI

      10.1039/c2cc16360h

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Metal-free α-CH amination of ethers with hypervalent sulfonylimino-λ3-bromane that acts as an active nitrenoid species at room temperature2012

    • Author(s)
      Ochiai M. et al.
    • Journal Title

      Chem. Commun.

      Volume: 48 Issue: 43 Pages: 5280-5282

    • DOI

      10.1039/c2cc31523h

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Presentation] Chemistry of Hypervalent Organoiodane(III) and Bromane(III)2012

    • Author(s)
      Masahito Ochiai
    • Organizer
      Sixth International Meeting on Halogen Chemistry, Indian Institute of Science
    • Place of Presentation
      Bangalore (India), Indian Institute of Science
    • Year and Date
      2012-12-10
    • Related Report
      2012 Final Research Report
  • [Presentation] モハメド マブブル ホク, 、超原子価ブロマン(III)を用いた不活性アルカンのケトンへの直接酸化反応2012

    • Author(s)
      宮本和範, 落合正仁
    • Organizer
      第38回反応と合成の進歩シンポジウム
    • Place of Presentation
      タワーホール船堀(東京都)
    • Year and Date
      2012-11-06
    • Related Report
      2012 Final Research Report
  • [Presentation] ヨードニウムイリドのヨードアレーンへのトランスイリド化反応2012

    • Author(s)
      岡田拓也、宮本和範、多田教浩、落合正仁
    • Organizer
      第15回ヨウ素学会シンポジウム
    • Place of Presentation
      千葉大学けやき会館(千葉県)
    • Year and Date
      2012-09-11
    • Related Report
      2012 Final Research Report
  • [Presentation] Aziridination of Olefins with Hypervalent Imino-・3-bromane Generated In Situ from (Diacetoxybromo)benzene under Metal-Free Conditions2012

    • Author(s)
      Md. Mahbubul Hoque, Kazunori Miyamoto, Norihiro Tada, Motoo Shiro, Masahito Ochiai
    • Organizer
      The 10th International Conference on Heteroatom Chemistry
    • Place of Presentation
      Uji Obaku Plaza (Kyoto-Fu)
    • Year and Date
      2012-05-21
    • Related Report
      2012 Final Research Report
  • [Presentation] Thermal Nucleophilic Aromatic Substitution of Diaryl-・3-bromanes2012

    • Author(s)
      Hiroki Yamashita, Kazunori Miyamoto, Masahito Ochiai, Satoko Hayashi, Waro Nakanishi
    • Organizer
      The 10th International Conference on Heteroatom Chemistry
    • Place of Presentation
      Uji Obaku Plaza (Kyoto-Fu)
    • Year and Date
      2012-05-21
    • Related Report
      2012 Final Research Report
  • [Presentation] Catalytic Version of Hypervalent Aryl-・3-iodane-Induced Hofmann Rearrangement of Primary Carboxamides2012

    • Author(s)
      Yuuta Sakai, Shunsuke Goda, Kazunori Miyamoto, Masahito Ochiai
    • Organizer
      The 10th International Conference on Heteroatom Chemistry
    • Place of Presentation
      Uji Obaku Plaza (Kyoto-Fu)
    • Year and Date
      2012-05-21
    • Related Report
      2012 Final Research Report
  • [Presentation] Aziridination of Olefins with Hypervalent Imino-λ3-bromane Generated In Situ from (Diacetoxybromo)benzene under Metal-Free Conditions2012

    • Author(s)
      Md. Mahbubul Hoque
    • Organizer
      The 10th International Conference on Heteroatom Chemistry
    • Place of Presentation
      京都大学(京都府)
    • Related Report
      2012 Annual Research Report
  • [Presentation] Thermal Nucleophilic Aromatic Substitution of Diaryl-λ3-bromanes2012

    • Author(s)
      Hiroki Yamashita
    • Organizer
      The 10th International Conference on Heteroatom Chemistry
    • Place of Presentation
      京都大学(京都府)
    • Related Report
      2012 Annual Research Report
  • [Presentation] Catalytic Version of Hypervalent Aryl-λ3-iodane-Induced Hofmann Rearrangement of Primary Carboxamides2012

    • Author(s)
      Yuuta Sakai
    • Organizer
      The 10th International Conference on Heteroatom Chemistry
    • Place of Presentation
      京都大学(京都府)
    • Related Report
      2012 Annual Research Report
  • [Presentation] Thermal Decomposition of Bis(perfluoroalkanesulfonyl)bromonium Ylides in Alkenes: Generation of Intramolecularly Stabilized Carbene That Is Singlet2012

    • Author(s)
      Susumu Iwasaki
    • Organizer
      The 10th International Conference on Heteroatom Chemistry
    • Place of Presentation
      京都大学(京都府)
    • Related Report
      2012 Annual Research Report
  • [Presentation] Synthesis, Structure, and Reaction of Br-Hydroxybenzbromoxolone2012

    • Author(s)
      Motomichi Saito
    • Organizer
      The 10th International Conference on Heteroatom Chemistry
    • Place of Presentation
      京都大学(京都府)
    • Related Report
      2012 Annual Research Report
  • [Presentation] Amination of Alkanes and Aziridination of Olefins with Iminobromane(III) under Metal-Free Conditions2012

    • Author(s)
      Masahito Ochiai
    • Organizer
      The 13th Belgian Organic Synthesis Symposium
    • Place of Presentation
      KU Leuven (Leuven, Belgium)
    • Related Report
      2012 Annual Research Report
  • [Presentation] 超原子価ブロマン(III)を用いた不活性アルカンのケトンへの直接酸化反応2012

    • Author(s)
      宮本和範
    • Organizer
      第38回反応と合成の進歩シンポジウム
    • Place of Presentation
      東京理科大学(東京都)
    • Related Report
      2012 Annual Research Report
  • [Presentation] ジアセトキシブロマン(III)を用いた芳香族C-Hアミノ化反応2012

    • Author(s)
      合田峻輔
    • Organizer
      第51回日本薬学会中四国支部大会
    • Place of Presentation
      島根県民会館(島根県)
    • Related Report
      2012 Annual Research Report
  • [Presentation] 超原子価ジアセトキシブロマンを用いたアルカンC-Hアミノ化反応2012

    • Author(s)
      太田泰雅
    • Organizer
      第51回日本薬学会中四国支部大会
    • Place of Presentation
      島根県民会館(島根県)
    • Related Report
      2012 Annual Research Report
  • [Presentation] 環状ブロモシルベンゼンを用いたオレフィンのエポキシ化反応2012

    • Author(s)
      齋藤基道
    • Organizer
      第51回日本薬学会中四国支部大会
    • Place of Presentation
      島根県民会館(島根県)
    • Related Report
      2012 Annual Research Report
  • [Presentation] Chemistry of Hypervalent Organoiodane(III) and Bromane(III)2012

    • Author(s)
      Masahito Ochiai
    • Organizer
      Sixth International Meeting on Halogen Chemistry
    • Place of Presentation
      Indian Institute of Science (Bangalore, India)
    • Related Report
      2012 Annual Research Report
    • Invited
  • [Presentation] ヨードニウムイリドのヨードアレーンへのトランスイリド化反応

    • Author(s)
      岡田拓也
    • Organizer
      第15回ヨウ素学会シンポジウム
    • Place of Presentation
      千葉大学(千葉県)
    • Related Report
      2012 Annual Research Report
  • [Remarks] 徳島大学薬学部薬品製造化学

    • URL

      http://www.tokushima-u.ac.jp/ph/faculty/labo/org/

    • Related Report
      2012 Final Research Report
  • [Remarks] 徳島大学薬学部薬品製造化学

    • URL

      http://www.tokushima-u.ac.jp/ph/faculty/labo/org/

    • Related Report
      2012 Annual Research Report

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Published: 2013-05-31   Modified: 2019-07-29  

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